Faculty of Pharmaceutical Sciences, Tokyo University of Science, 2641 Yamazaki, Noda, Chiba, Japan,
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- Χρύσης Αναστασιάδης
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1 Supporting information Regioselective Aromatic Substitution Reactions of Cyclometalated Ir(III) Complexes: Synthesis and Photochemical Properties of Substituted Ir(III) Complexes that Exhibit Blue, Green, and Red Color Luminescence Emission Shin Aoki, *,, Yasuki Matsuo, Shiori Ogura, Hiroki Ohwada, Yosuke Hisamatsu, Shinnsuke Moromizato, Motoo Shiro, and Masanori Kitamura, Faculty of Pharmaceutical Sciences, Tokyo University of Science, 2641 Yamazaki, Noda, Chiba, Japan, Center for Technologies against Cancer (CTC), Tokyo University of Science, 2641 Yamazaki, Noda, Chiba, Japan, and Rigaku Corporation, X-ray Research Laboratory, Matsubaracho, Akishima, Tokyo, Japan. *To whom correspondence should be addressed. RECEIVED DATE (to be automatically inserted after your manuscript is accepted if required according to the journal that you are submitting your paper to) Faculty of Pharmaceutical Sciences, Tokyo University of Science Center for Technologies against Cancer (CTC), Tokyo University of Science Rigaku Corporation, X-ray Research Laboratory 1
2 (a) ArH(6') ArH(3') ArH(5') Me(4') (b) ArH(6') ArH(3') Me(4') (c) Relative intensity (%) δ (ppm) Figure S1. (a) 1 H NMR spectra of 1 in CDCl 3 (300MHz/TMS) before bromination, (b) 1 H NMR spectra of the brominated Ir(tpy) 3 complex 3a in CDCl 3 (300MHz/TMS). The aliphatic (right) and aromatic (left) regions are shown. For assignments, see Chart 2. (c) Mass spectrum of 3a. m/z 2
3 (a) Me I I Me Ir Me I (b) I Me I Me Me I Ir Figure S2. Top view (a) and side view (b) of stick drawings of 3b (Ir(5 -I-tpy) 3 ). The three tpy units are shown in light blue, green-yellow, and light green, Ir in red, and I in blue.. 3
4 (a) 3' 5' (b) 3' 5' Figure S3. The results of DFT calculation of HOMO (B3LYP/LanL2DZ) of 2, (a) top view and (b) side view. 4
5 (a) 600 Emission intensity (a.u.) a 5 3b Wavelength (nm) (b) Emission intensity (a.u.) Wavelength (nm) Figure S4. (a) Excitation spectra of 1 (plain curve), 3a (bold curve), 3b (dashed curve), and 7 (bold dashed curve) in degassed CH 2 Cl 2 at 25 C (emission at 486 nm). (b) Excitation spectra of 1 (plain curve), 7 (bold curve), 10 (thin curve), 19 (dashed curve), and 22 (bold dashed curve) in degassed CH 2 Cl 2 at 25 C (emission at 486 nm). [Ir complex] = 10 μm. A.u. is in arbitrary units. 5
6 ε 10-4 (l cm -1 mol -1 ) (a) (c) (b) Wavelength (nm) Figure S5. UV spectra of (a) benzaldehyde (plain curve), (b) anisaldehyde (bold curve) and (c) anisole (dashed curve) in CH 2 Cl 2 at 25 C 6
7 (a) Emission intensity (a.u.) EtOH MeCN 1,4-dioxane CH 2 Cl 2 DMSO DMSO/H 2 O (1/6) (b) Wavelength (nm) Solvent Emission of 12 ε N r E T λ em (nm) Φ DMSO acetone MeCN 1,4-dioxane MeOH EtOH CH 2 Cl 2 DMSO/H 2 O (1/6) (for H 2 O) (for H 2 O) Figure S6. (a) Emission spectra of 12 in DMSO, DMSO/H 2 O (1/6), MeCN, 1,4-dioxane, EtOH, and CH 2 Cl 2 at 25 C. All solutions except DMSO include 0.3% DMSO. [Ir complex] = 10 μm. Excitation at 366 nm. A.u. is in arbitrary units. (b) Emission maxima (nm) and quantum yields (Φ) of 12 in DMSO, DMSO/H 2 O (1/6), acetone, MeCN, 1,4-dioxane, MeOH, EtOH, and CH 2 Cl 2. All solutions except DMSO include 0.3% DMSO for solvation of 12. [Ir complex] = 10 μm. Excitation at 366 nm. Physical parameters of solvents (dielectric constants (ε r ) and normalized empirical parameters of solvent polarity (E N T ) based on the intramolecualr charge transfer absorption of a pyridinium-n-phenoxide betaine dye) were taken from (a) Reichardt, C. Solvents and Solvent Effects in Organic Chemistry, 2nd Ed. VCH: Germany, (b) Marcus, Y. The Properties of Solvents. John Wiley & Sons: Chichster,
8 Absorbance H Wavelength (nm) 600 Figure S7. UV spectra of 12 and H 3 12 (prepared by 12 + HCl (excess) in 1,4-dioxane) in CH 2 Cl 2 at 25 C. [Ir complex] = 10 μm. 8
9 (a) (b) (c) Current 10-5 ( A) Current 10-5 (A) Potential (V) vs. Ag/AgCl Potential (V) vs. Ag/AgCl Current 10-5 ( A) Potential (V) vs. Ag/AgCl Figure S8. Typical cyclic voltammetry (CV) curves of (a) 1 (b) 22, and (c) 12 recorded (on a glassy carbon electrode at a scan rate of 100 mv sec 1 ) in DMF containing 0.1 mm (nbu) 4 N(PF 6 ) vs Ag/AgCl at 25 C [Ir complex] = 1 mm. 9
10 E 1/2 ox or E p ox (V) a E 1/2 red or E p red (V) a ΔE 1 (V) b PhCN Ir N Me R 22 (R = CN) 1 (R = H) (irreversible) (irreversible) (irreversible) (irreversible) (irreversible) (irreversible) (R = NH 2 ) (irreversible) (irreversible) (irreversible) (irreversible) (irreversible) 2.63 PhNH (irreversible) (irreversible) a E 1/2 : half-wave potential, E p : peak potential, b ΔE 1 (V) = E ox E red (1st) Figure S9. The summary of potential gaps between the first oxidation and reduction of benzonitrile, 22, 1, 12, and aniline, in DMF containing 0.1 M (nbu) 4 N(PF 6 ) at 25 C determined by CV curves shown in Figure S8. 10
11 Absorbance ph 3 ph 4 ph 5 ph 6 ph 7 ph 8 Absorbance Abs at 280 nm Abs at 400 nm ph Wavelength (nm) 600 Figure S10. ph-dependent change in UV/vis spectra of 12 in DMSO/100 mm buffer (from ph 3 to 8) at 25 C. [Ir complex] = 10 μm. (Inset) The ph-dependent (ph 3~10) change of absorbance of 12 at 280 nm and 400 nm. 11
12 (a) eq. MeSO 3 H eq. MeSO 3 H eq. MeSO 3 H eq. MeSO 3 H Emission intensity (a.u.) eq. MeSO 3 H eq. MeSO 3 H 12 before addition of acid (λ max = 586 nm) (b) Wavelength (nm) with MeSO 3 H Emission intensity at 515 nm (a.u.) with aq. HCl with TFA with ClH 2 CCO 2 H [Acid] / [12] Figure S11. (a) Change of luminescence spectra of 12 (100 μm) upon addition of methanesulfonic acid (MeSO 3 H) in DMSO at 25 C. A.u. is an arbitrary unit. (b) Results of luminescence titrations (at 515 nm) of 12 (100 μm) with ClCH 2 CO 2 H (closed square), CF 3 CO 2 H (open circle), 0.1 M aq. HCl (closed circle), and MeSO 3 H (open square) in DMSO at 25 C. Excitation at 366 nm. 12
13 Table S1. The Parameters for X-ray Crystal Structure Analysis of 3a. Formula C H Br 3 Cl 3.54 Ir N 3 Mr Crystal system Cubic space group P2 1 3(#198) a (Å) (4) b (Å) (4) c (Å) (4) V (Å 3 ) (4) Z 12 D calc (g cm 3 ) μ (MoKα) (cm 1 ) R1 (I > 2σ(I)) wr2 (all reflections) No. of unique reflections 7069 (2θ < 57.4 ) The structure was solved by direct method and refined using least squares techniques (SHELXL97). 13
14 Table S2. Selected Bond Lengths of 3a. length (Å) length (Å) Ir(1) C(11) 2.013(8) Ir(1) N(1) 2.129(6) Ir(2) C(24) 2.032(7) Ir(2) N(2) 2.128(6) Ir(3) C(35) 2.011(8) Ir(3) N(3) 2.117(6) Br(1) C(8) 1.911(9) Br(2) C(20) 1.898(7) Br(3) C(32) 1.913(7) Cl(1) C(37) 1.766(7) Cl(2) C(38) 1.73(2) Cl(2) Cl(4) 2.444(13) Cl(3) C(39) 1.76(2) Cl(4) C(39) 1.782(19) Cl(5) C(39) 1.783(17) N(1) C(1) 1.353(10) N(1) C(5) 1.375(9) N(2) C(13) 1.339(9) N(2) C(17) 1.358(9) N(3) C(25) 1.343(9) N(3) C(29) 1.385(9) C(1) C(2) 1.378(11) C(2) C(3) 1.384(11) C(3) C(4) 1.383(12) C(4) C(5) 1.396(11) C(5) C(6) 1.443(11) C(6) C(7) 1.384(12) C(6) C(11) 1.433(11) C(7) C(8) 1.375(13) C(8) C(9) 1.388(14) C(9) C(10) 1.397(13) C(9) C(12) 1.528(12) C(10) C(11) 1.405(11) C(13) C(14) 1.344(11) C(14) C(15) 1.406(12) C(15) C(16) 1.385(11) 14
15 C(16) C(17) 1.396(10) C(17) C(18) 1.464(10) C(18) C(19) 1.387(10) C(18) C(24) 1.418(9) C(19) C(20) 1.385(12) C(20) C(21) 1.388(12) C(21) C(22) 1.395(11) C(21) C(23) 1.494(11) C(22) C(24) 1.382(10) C(25) C(26) 1.381(11) C(26) C(27) 1.382(12) C(27) C(28) 1.390(11) C(28) C(29) 1.376(10) C(29) C(30) 1.481(10) C(30) C(31) 1.398(10) C(30) C(35) 1.404(10) C(31) C(32) 1.376(11) C(32) C(33) 1.361(12) C(33) C(34) 1.408(11) C(33) C(36) 1.538(11) C(34) C(35) 1.405(11) C(37) Cl(1) 1.766(7) C(38) Cl(2) 1.73(2) 15
16 Table S3. Selected Bond Angles ( ) of 3a angle ( ) angle ( ) C(11) Ir(1) C(11) 95.0(3) C(11) Ir(1) C(11) 95.0(3) C(11) Ir(1) C(11) 95.0(3) C(11) Ir(1) N(1) 79.3(3) C(11) Ir(1) N(1) 91.6(3) C(11) Ir(1) N(1) 171.7(3) C(11) Ir(1) N(1) 91.6(3) C(11) Ir(1) N(1) 171.7(3) C(11) Ir(1) N(1) 79.3(3) N(1) Ir(1) N(1) 94.7(2) C(11) Ir(1) N(1) 171.7(3) C(11) Ir(1) N(1) 79.3(3) C(11) Ir(1) N(1) 91.6(3) N(1) Ir(1) N(1) 94.7(2) N(1) Ir(1) N(1) 94.6(2) C(24) Ir(2) C(24) 94.7(2) C(24) Ir(2) C(24) 94.7(2) C(24) Ir(2) C(24) 94.7(2) C(24) Ir(2) N(2) 79.9(2) C(24) Ir(2) N(2) 88.7(2) C(24) Ir(2) N(2) 173.9(2) C(24) Ir(2) N(2) 173.9(2) C(24) Ir(2) N(2) 79.9(2) C(24) Ir(2) N(2) 88.7(2) N(2) Ir(2) N(2) 96.9(2) C(24) Ir(2) N(2) 88.7(2) C(24) Ir(2) N(2) 173.9(2) C(24) Ir(2) N(2) 79.9(2) N(2) Ir(2) N(2) 96.9(2) N(2) Ir(2) N(2) 96.9(2) C(35) Ir(3) C(35) 97.5(3) C(35) Ir(3) C(35) 97.5(3) C(35) Ir(3) C(35) 97.5(3) C(35) Ir(3) N(3) 79.5(3) 16
17 C(35) Ir(3) N(3) 89.6(2) C(35) Ir(3) N(3) 172.6(3) C(35) Ir(3) N(3) 172.6(3) C(35) Ir(3) N(3) 79.5(3) C(35) Ir(3) N(3) 89.6(3) N(3) Ir(3) N(3) 93.8(2) C(35) Ir(3) N(3) 89.6(2) C(35) Ir(3) N(3) 172.6(3) C(35) Ir(3) N(3) 79.5(3) N(3) Ir(3) N(3) 93.8(2) N(3) Ir(3) N(3) 93.8(2) C(38) Cl(2) Cl(4) 172.9(16) C(39) Cl(4) Cl(2) 153.5(8) C(1) N(1) C(5) 119.0(6) C(1) N(1) Ir(1) 126.3(5) C(5) N(1) Ir(1) 114.7(5) C(13) N(2) C(17) 119.6(6) C(13) N(2) Ir(2) 126.0(5) C(17) N(2) Ir(2) 114.1(4) C(25) N(3) C(29) 118.0(6) C(25) N(3) Ir(3) 126.6(5) C(29) N(3) Ir(3) 115.4(5) N(1) C(1) C(2) 122.3(7) C(1) C(2) C(3) 120.0(7) C(4) C(3) C(2) 117.8(7) C(3) C(4) C(5) 121.4(7) N(1) C(5) C(4) 119.5(7) N(1) C(5) C(6) 114.4(6) C(4) C(5) C(6) 126.1(7) C(7) C(6) C(11) 121.3(8) C(7) C(6) C(5) 122.5(8) C(11) C(6) C(5) 116.3(7) C(8) C(7) C(6) 119.8(9) C(7) C(8) C(9) 121.7(8) C(7) C(8) Br(1) 117.7(7) C(9) C(8) Br(1) 120.4(7) C(8) C(9) C(10) 118.5(8) C(8) C(9) C(12) 122.1(9) C(10) C(9) C(12) 119.4(9) C(9) C(10) C(11) 122.3(9) 17
18 C(10) C(11) C(6) 116.5(7) C(10) C(11) Ir(1) 128.2(6) C(6) C(11) Ir(1) 115.3(5) N(2) C(13) C(14) 124.0(7) C(13) C(14) C(15) 118.3(7) C(16) C(15) C(14) 118.4(7) C(15) C(16) C(17) 120.4(7) N(2) C(17) C(16) 119.2(6) N(2) C(17) C(18) 114.8(6) C(16) C(17) C(18) 126.0(7) C(19) C(18) C(24) 119.8(7) C(19) C(18) C(17) 123.3(7) C(24) C(18) C(17) 116.8(6) C(20) C(19) C(18) 119.3(7) C(19) C(20) C(21) 122.9(7) C(19) C(20) Br(2) 119.6(6) C(21) C(20) Br(2) 117.4(6) C(20) C(21) C(22) 116.4(7) C(20) C(21) C(23) 123.7(7) C(22) C(21) C(23) 119.8(7) C(24) C(22) C(21) 123.2(7) C(22) C(24) C(18) 118.3(7) C(22) C(24) Ir(2) 127.8(5) C(18) C(24) Ir(2) 113.9(5) N(3) C(25) C(26) 123.2(7) C(25) C(26) C(27) 119.1(8) C(26) C(27) C(28) 118.4(7) C(29) C(28) C(27) 120.7(7) C(28) C(29) N(3) 120.6(7) C(28) C(29) C(30) 127.0(6) N(3) C(29) C(30) 112.5(6) C(31) C(30) C(35) 123.4(7) C(31) C(30) C(29) 120.0(6) C(35) C(30) C(29) 116.6(6) C(32) C(31) C(30) 118.5(7) C(33) C(32) C(31) 121.6(7) C(33) C(32) Br(3) 121.1(6) C(31) C(32) Br(3) 117.2(6) C(32) C(33) C(34) 118.7(7) C(32) C(33) C(36) 122.3(7) 18
19 C(34) C(33) C(36) 118.9(7) C(35) C(34) C(33) 123.0(7) C(30) C(35) C(34) 114.7(7) C(30) C(35) Ir(3) 115.9(5) C(34) C(35) Ir(3) 129.3(6) Cl(1) C(37) Cl(1) 110.1(6) Cl(1) C(37) Cl(1) 110.1(6) Cl(1) C(37) Cl(1) 110.1(6) Cl(2) C(38) Cl(2) 112(2) Cl(2) C(38) Cl(2) 112(2) Cl(2) C(38) Cl(2) 112(2) Cl(3) C(39) Cl(4) 107.2(9) Cl(3) C(39) Cl(5) 110.0(9) Cl(4) C(39) Cl(5) 110.3(10) 19
20 Table S4. CIF for the 3a data_general _audit_creation_date ' ' _audit_creation_method 'by CrystalStructure 3.8' _audit_update_record? #================================================================== ============ # PROCESSING SUMMARY (IUCr Office Use Only) _journal_date_recd_electronic? _journal_date_from_coeditor? _journal_date_accepted? _journal_coeditor_code? #================================================================== ============ # SUBMISSION DETAILS _publ_contact_author_name 'ENTER NAME' _publ_contact_author_ 'ENTER ADDRESS' _publ_contact_author_fax 'ENTER FAX NUMBER' _publ_contact_author_phone 'ENTER PHONE NUMBER' _publ_contact_letter ENTER TEXT OF LETTER _publ_requested_journal test _publ_requested_category 'CHOOSE FI FM FO CI CM CO or AD' _publ_requested_coeditor_name? #================================================================== ============ # TITLE AND AUTHOR LIST _publ_section_title ENTER SECTION TITLE _publ_section_title_footnote ENTER FOOTNOTE TO TITLE OF PAPER loop publ_author_name _publ_author_footnote _publ_author_address ' FIRST AUTHORS NAME ' FIRST AUTHORS FOOTNOTES FIRST AUTHORS ADDRESS _publ_section_synopsis ENTER SYNOPSIS 20
21 #================================================================== ============ # TEXT _publ_section_abstract ENTER ABSTRACT _publ_section_comment ENTER TEXT _publ_section_references ENTER OTHER REFERENCES Johnson, C.K. (1976). ORTEP-II. A FORTRAN Thermal-Ellipsoid Plot Program. Report ORNL Oak Ridge National Laboratory, Tennessee, USA. Rigaku (1998). PROCESS-AUTO. Automatic Data Acquisition and Processing Package for Imaging Plate Diffractometer. Rigaku Corporation, Tokyo , Japan Rigaku & RAC (2007). CrystalStructure (Version 3.80). Single Crystal Structure Analysis Software. Rigaku, Tokyo , Japan. Rigaku Americas, TX, USA Sheldrick, G.M. (1997). SHELXS97. Program for the Solution of Crystal Structures. University of Gottingen, Germany. Sheldrick, G.M. (1997). SHELXL97. University of Gottingen, Germany. _publ_section_figure_captions ENTER FIGURE CAPTIONS _publ_section_exptl_prep ENTER COMPOUND PREPARATION DETAILS _publ_section_exptl_refinement ENTER SPECIAL DETAILS OF THE REFINEMENT #================================================================== ============ data RGK1363 #================================================================== ============ # CHEMICAL DATA _chemical_formula_sum 'C37.18 H28.18 Br3 Cl3.54 Ir N3 ' 21
22 _chemical_formula_moiety 'C36 H27 Br3 Ir N3, 1.18(C H Cl3) ' _chemical_formula_weight _chemical_melting_point? _chemical_absolute_configuration ad #================================================================== ============ # CRYSTAL DATA _symmetry_cell_setting cubic _symmetry_space_group_name_h-m 'P 21 3' _symmetry_space_group_name_hall 'P 2ac 2ab 3' _symmetry_int_tables_number 198 loop symmetry_equiv_pos_as_xyz 'x, y, z' 'y, z, x' 'z, x, y' 'x+1/2, -y+1/2, -z' 'y+1/2, -z+1/2, -x' 'z+1/2, -x+1/2, -y' '-y, z+1/2, -x+1/2' '-z, x+1/2, -y+1/2' '-z+1/2, -x, y+1/2' '-x+1/2, -y, z+1/2' '-y+1/2, -z, x+1/2' '-x, y+1/2, -z+1/2' # _cell_length_a (4) _cell_length_b (4) _cell_length_c (4) _cell_angle_alpha _cell_angle_beta _cell_angle_gamma _cell_volume (4) _cell_formula_units_z 12 _cell_measurement_reflns_used _cell_measurement_theta_min 3.4 _cell_measurement_theta_max 26.0 _cell_measurement_temperature # _exptl_crystal_description 'platelet' _exptl_crystal_colour 'yellow' _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.07 _exptl_crystal_density_diffrn _exptl_crystal_density_meas? _exptl_crystal_density_method 'not measured' _exptl_crystal_f_ _exptl_absorpt_coefficient_mu _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. 22
23 _exptl_absorpt_correction_t_min _exptl_absorpt_correction_t_max #================================================================== ============ # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K a' _diffrn_radiation_wavelength _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method w _diffrn_detector_area_resol_mean _diffrn_reflns_number _diffrn_reflns_av_r_equivalents _diffrn_reflns_theta_max _diffrn_measured_fraction_theta_max _diffrn_reflns_theta_full _diffrn_measured_fraction_theta_full _diffrn_ambient_temperature _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 #================================================================== ============ # REFINEMENT DATA _refine_special_details Refinement was performed using all reflections. The weighted R-factor (wr) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(f^2^) is used only for calculating R-factor (gt). _reflns_number_total 7069 _reflns_number_gt 6945 _reflns_threshold_expression F^2^>2.0 s(f^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_r_factor_gt _refine_ls_wr_factor_ref _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 7069 _refine_ls_number_parameters 452 _refine_ls_goodness_of_fit_ref _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[ s^2^(fo^2^)+(0.0543p)^2^ p] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_shift/su_max _refine_diff_density_max 1.87 _refine_diff_density_min _refine_ls_extinction_method none _refine_ls_extinction_coef? _refine_ls_abs_structure_details 'Flack, H. D. (1983), Acta Cryst. A39, Friedel Pairs' _refine_ls_abs_structure_flack 0.03(1) 23
24 loop atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' International Tables for Crystallography (1992, Vol. C, Tables and ) 'H' 'H' International Tables for Crystallography (1992, Vol. C, Table ) 'Br' 'Br' International Tables for Crystallography (1992, Vol. C, Tables and ) 'Cl' 'Cl' International Tables for Crystallography (1992, Vol. C, Tables and ) 'Ir' 'Ir' International Tables for Crystallography (1992, Vol. C, Tables and ) 'N' 'N' International Tables for Crystallography (1992, Vol. C, Tables and ) #================================================================== ============ # ATOMIC COORDINATES AND THERMAL PARAMETERS loop atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_u_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ir1 Ir (11) (11) (11) (11) Uani 1 3 d S.. Ir2 Ir (11) (11) (11) (11) Uani 1 3 d S.. Ir3 Ir (11) (11) (11) (11) Uani 1 3 d S.. Br1 Br (6) (7) (5) (4) Uani 1 1 d... Br2 Br (4) (5) (6) (3) Uani 1 1 d... 24
25 Br3 Br (5) (4) (4) (2) Uani 1 1 d... N1 N (3) (3) (2) (12) Uani 1 1 d... N2 N (3) (2) (2) (12) Uani 1 1 d... N3 N (3) (3) (3) (12) Uani 1 1 d... C1 C (3) (3) (4) (15) Uani 1 1 d... H1 H Uiso 1 1 calc R.. C2 C (3) (3) (3) (16) Uani 1 1 d... H2 H Uiso 1 1 calc R.. C3 C (4) (4) (4) (18) Uani 1 1 d... H3 H Uiso 1 1 calc R.. C4 C (3) (3) (3) (15) Uani 1 1 d... H4 H Uiso 1 1 calc R.. C5 C (3) (3) (3) (15) Uani 1 1 d... C6 C (3) (4) (3) (16) Uani 1 1 d... C7 C (4) (4) (4) (19) Uani 1 1 d... H5 H Uiso 1 1 calc R.. C8 C (4) (4) (4) 0.045(2) Uani 1 1 d... C9 C (4) (4) (4) 0.047(2) Uani 1 1 d... C10 C (4) (4) (4) (19) Uani 1 1 d... H6 H Uiso 1 1 calc R.. C11 C (3) (3) (4) (16) Uani 1 1 d... C12 C (5) (5) (5) 0.059(3) Uani 1 1 d... H7 H Uiso 1 1 calc R.. H8 H Uiso 1 1 calc R.. H9 H Uiso 1 1 calc R.. C13 C (3) (3) (3) (15) Uani 1 1 d... H10 H Uiso 1 1 calc R.. C14 C (4) (4) (4) (17) Uani 1 1 d... H11 H Uiso 1 1 calc R.. C15 C (4) (3) (3) (17) Uani 1 1 d... H12 H Uiso 1 1 calc R.. C16 C (3) (3) (4) (16) Uani 1 1 d... H13 H Uiso 1 1 calc R.. C17 C (3) (3) (3) (14) Uani 1 1 d... C18 C (3) (3) (3) (14) Uani 1 1 d... C19 C (4) (4) (4) (19) Uani 1 1 d... H14 H Uiso 1 1 calc R.. C20 C (3) (4) (4) (19) Uani 1 1 d... C21 C (3) (4) (3) (16) Uani 1 1 d... C22 C (3) (3) (3) (15) Uani 1 1 d... H15 H Uiso 1 1 calc R.. C23 C (4) (4) (4) 0.044(2) Uani 1 1 d... H16 H Uiso 1 1 calc R.. H17 H Uiso 1 1 calc R.. H18 H Uiso 1 1 calc R.. C24 C (3) (3) (3) (14) Uani 1 1 d... C25 C (3) (3) (3) (15) Uani 1 1 d... H19 H Uiso 1 1 calc R.. C26 C (4) (4) (4) (18) Uani 1 1 d... H20 H Uiso 1 1 calc R.. C27 C (4) (4) (3) (17) Uani 1 1 d... H21 H Uiso 1 1 calc R.. C28 C (3) (3) (3) (16) Uani 1 1 d... H22 H Uiso 1 1 calc R.. C29 C (3) (3) (3) (14) Uani 1 1 d... C30 C (3) (3) (3) (13) Uani 1 1 d... C31 C (3) (3) (3) (15) Uani 1 1 d... H23 H Uiso 1 1 calc R.. C32 C (4) (3) (4) (18) Uani 1 1 d... C33 C (3) (4) (4) (17) Uani 1 1 d... C34 C (3) (4) (3) (17) Uani 1 1 d... 25
26 H24 H Uiso 1 1 calc R.. C35 C (3) (3) (3) (15) Uani 1 1 d... C36 C (4) (4) (5) 0.044(2) Uani 1 1 d... H25 H Uiso 1 1 calc R.. H26 H Uiso 1 1 calc R.. H27 H Uiso 1 1 calc R.. C37 C (5) (5) (5) 0.063(5) Uani 1 3 d S.. H28 H Uiso 1 3 calc SR.. Cl1 Cl (14) (15) (16) (8) Uani 1 1 d... C38 C (19) (19) (19) 0.047(9) Uani 0.228(6) 3 d SPU A 1 H29 H Uiso 0.228(6) 3 calc SPR A 1 Cl2 Cl (5) (5) (5) 0.055(3) Uani 0.228(6) 1 d PU A 1 C39 C (8) (8) (7) 0.075(5) Uani 0.772(6) 1 d P A 2 H30 H Uiso 0.772(6) 1 calc PR A 2 Cl3 Cl (2) (2) (2) (15) Uani 0.772(6) 1 d P A 2 Cl4 Cl (2) (4) (3) 0.123(3) Uani 0.772(6) 1 d P A 2 Cl5 Cl (15) (16) (2) (11) Uani 0.772(6) 1 d P A 2 loop atom_site_aniso_label _atom_site_aniso_u_11 _atom_site_aniso_u_22 _atom_site_aniso_u_33 _atom_site_aniso_u_23 _atom_site_aniso_u_13 _atom_site_aniso_u_12 Ir (11) (11) (11) (10) (10) (10) Ir (11) (11) (11) (10) (10) (10) Ir (11) (11) (11) (10) (10) (10) Br (9) (10) (5) (5) (5) (7) Br (4) (5) (9) (6) (5) (4) Br (5) (4) (5) (4) (4) (4) Cl (17) (18) 0.086(2) (16) (15) (14) Cl (6) 0.063(6) 0.051(6) (5) (4) (5) Cl (3) 0.079(3) 0.082(3) 0.026(2) 0.035(2) 0.030(2) Cl (3) 0.194(7) 0.096(4) 0.046(4) 0.017(3) (4) Cl (19) 0.060(2) 0.098(3) 0.005(2) (19) (16) N (3) 0.032(3) 0.020(3) (2) 0.000(2) (2) N (3) 0.025(3) 0.023(3) 0.003(2) 0.001(2) 0.000(2) N (3) 0.022(3) 0.024(3) 0.005(2) 0.001(2) (2) C (3) 0.027(3) 0.034(4) (3) 0.003(3) (3) C (4) 0.030(4) 0.036(4) 0.001(3) 0.000(3) (3) C (4) 0.033(4) 0.046(5) (3) 0.012(4) (3) C (4) 0.038(4) 0.031(4) 0.002(3) 0.004(3) (3) C (3) 0.029(3) 0.030(4) (3) (3) (3) C (4) 0.037(4) 0.030(4) 0.000(3) (3) (3) C (4) 0.055(5) 0.034(4) 0.003(4) 0.006(4) (4) C (5) 0.058(5) 0.035(4) 0.013(4) 0.002(4) (4) C (5) 0.053(5) 0.045(5) 0.017(4) (4) (4) C (4) 0.040(4) 0.043(5) 0.005(4) (4) (4) C (3) 0.033(4) 0.042(4) 0.010(3) (3) (3) C (6) 0.052(6) 0.059(6) 0.034(5) 0.002(5) (5) C (4) 0.029(4) 0.023(3) (3) 0.003(3) (3) C (4) 0.033(4) 0.035(4) 0.002(3) 0.000(3) (3) C (5) 0.025(4) 0.036(4) (3) 0.003(4) (3) C (4) 0.025(3) 0.040(4) (3) 0.004(3) 0.000(3) C (3) 0.022(3) 0.020(3) 0.004(3) (3) 0.001(3) C (3) 0.028(3) 0.019(3) (3) 0.004(3) (3) C (4) 0.032(4) 0.055(5) (4) 0.013(4) 0.009(3) C (4) 0.051(5) 0.048(5) 0.001(4) 0.011(3) 0.008(3) C (4) 0.035(4) 0.028(4) 0.007(3) 0.000(3) (3) 26
27 C (4) 0.028(4) 0.032(4) (3) 0.000(3) (3) C (4) 0.050(5) 0.053(5) 0.005(4) 0.010(4) (4) C (3) 0.026(3) 0.019(3) 0.003(2) 0.000(3) (3) C (3) 0.031(4) 0.039(4) 0.009(3) (3) (3) C (4) 0.039(4) 0.047(5) 0.011(4) 0.002(4) 0.000(3) C (4) 0.042(4) 0.034(4) 0.008(3) 0.004(3) (3) C (4) 0.024(3) 0.032(4) 0.002(3) (3) (3) C (4) 0.016(3) 0.025(3) 0.001(3) (3) 0.000(3) C (3) 0.020(3) 0.024(3) 0.003(2) (3) (3) C (4) 0.023(3) 0.035(4) 0.002(3) (3) 0.000(3) C (4) 0.023(3) 0.051(5) 0.009(3) (4) 0.011(3) C (4) 0.036(4) 0.039(4) 0.005(3) 0.000(3) 0.009(3) C (4) 0.043(4) 0.030(4) 0.002(3) (3) 0.002(3) C (4) 0.030(4) 0.025(3) (3) (3) (3) C (4) 0.032(4) 0.067(6) 0.001(4) 0.002(4) 0.010(3) C (5) 0.063(5) 0.063(5) (5) (5) (5) C (9) 0.047(9) 0.047(9) 0.003(6) (6) 0.003(6) C (10) 0.091(12) 0.056(8) 0.034(8) 0.001(8) 0.021(9) #================================================================== ============ _computing_data_collection _computing_cell_refinement _computing_data_reduction _computing_structure_solution _computing_structure_refinement _computing_publication_material _computing_molecular_graphics 'PROCESS-AUTO (Rigaku, 1998)' 'PROCESS-AUTO (Rigaku, 1998)' 'CrystalStructure (Rigaku & RAC 2007)' 'SHELXS97 (Sheldrick, 1997)' 'SHELXL97 (Sheldrick, 1997)' 'CrystalStructure (Rigaku & RAC 2007)' 'ORTEP (Johnson, 1976)' #================================================================== ============ # MOLECULAR GEOMETRY _geom_special_details ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY loop geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ir1 C (8) 11_664? Ir1 C (8).? Ir1 C (8) 6_566? Ir1 N (6) 11_664? Ir1 N (6) 6_566? Ir1 N (6).? Ir2 C (7) 8_645? Ir2 C (7).? Ir2 C (7) 5_556? Ir2 N (6) 8_645? Ir2 N (6).? Ir2 N (6) 5_556? Ir3 C (8) 7_655? Ir3 C (8).? Ir3 C (8) 9_564? 27
28 Ir3 N (6) 7_655? Ir3 N (6).? Ir3 N (6) 9_564? Br1 C (9).? Br2 C (7).? Br3 C (7).? Cl1 C (7).? Cl2 C (2).? Cl2 Cl (13).? Cl3 C (2).? Cl4 C (19).? Cl5 C (17).? N1 C (10).? N1 C (9).? N2 C (9).? N2 C (9).? N3 C (9).? N3 C (9).? C1 C (11).? C2 C (11).? C3 C (12).? C4 C (11).? C5 C (11).? C6 C (12).? C6 C (11).? C7 C (13).? C8 C (14).? C9 C (13).? C9 C (12).? C10 C (11).? C13 C (11).? C14 C (12).? C15 C (11).? C16 C (10).? C17 C (10).? C18 C (10).? C18 C (9).? C19 C (12).? C20 C (12).? C21 C (11).? C21 C (11).? C22 C (10).? C25 C (11).? C26 C (12).? C27 C (11).? C28 C (10).? C29 C (10).? C30 C (10).? C30 C (10).? C31 C (11).? C32 C (12).? C33 C (11).? C33 C (11).? C34 C (11).? C37 Cl (7) 2? C37 Cl (7) 3? C38 Cl2 1.73(2) 6? C38 Cl2 1.73(2) 11_554? loop geom_angle_atom_site_label_1 28
29 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 Ir1 C (3) 11_664.? C11 Ir1 C (3) 11_664 6_566? C11 Ir1 C (3). 6_566? C11 Ir1 N1 79.3(3) 11_664 11_664? C11 Ir1 N1 91.6(3). 11_664? C11 Ir1 N (3) 6_566 11_664? C11 Ir1 N1 91.6(3) 11_664 6_566? C11 Ir1 N (3). 6_566? C11 Ir1 N1 79.3(3) 6_566 6_566? N1 Ir1 N1 94.7(2) 11_664 6_566? C11 Ir1 N (3) 11_664.? C11 Ir1 N1 79.3(3)..? C11 Ir1 N1 91.6(3) 6_566.? N1 Ir1 N1 94.7(2) 11_664.? N1 Ir1 N1 94.6(2) 6_566.? C24 Ir2 C (2) 8_645.? C24 Ir2 C (2) 8_645 5_556? C24 Ir2 C (2). 5_556? C24 Ir2 N2 79.9(2) 8_645 8_645? C24 Ir2 N2 88.7(2). 8_645? C24 Ir2 N (2) 5_556 8_645? C24 Ir2 N (2) 8_645.? C24 Ir2 N2 79.9(2)..? C24 Ir2 N2 88.7(2) 5_556.? N2 Ir2 N2 96.9(2) 8_645.? C24 Ir2 N2 88.7(2) 8_645 5_556? C24 Ir2 N (2). 5_556? C24 Ir2 N2 79.9(2) 5_556 5_556? N2 Ir2 N2 96.9(2) 8_645 5_556? N2 Ir2 N2 96.9(2). 5_556? C35 Ir3 C (3) 7_655.? C35 Ir3 C (3) 7_655 9_564? C35 Ir3 C (3). 9_564? C35 Ir3 N3 79.5(3) 7_655 7_655? C35 Ir3 N3 89.6(2). 7_655? C35 Ir3 N (3) 9_564 7_655? C35 Ir3 N (3) 7_655.? C35 Ir3 N3 79.5(3)..? C35 Ir3 N3 89.6(3) 9_564.? N3 Ir3 N3 93.8(2) 7_655.? C35 Ir3 N3 89.6(2) 7_655 9_564? C35 Ir3 N (3). 9_564? C35 Ir3 N3 79.5(3) 9_564 9_564? N3 Ir3 N3 93.8(2) 7_655 9_564? N3 Ir3 N3 93.8(2). 9_564? C38 Cl2 Cl (16)..? C39 Cl4 Cl (8)..? C1 N1 C (6)..? C1 N1 Ir (5)..? C5 N1 Ir (5)..? C13 N2 C (6)..? C13 N2 Ir (5)..? C17 N2 Ir (4)..? C25 N3 C (6)..? C25 N3 Ir (5)..? 29
30 C29 N3 Ir (5)..? N1 C1 C (7)..? C1 C2 C (7)..? C4 C3 C (7)..? C3 C4 C (7)..? N1 C5 C (7)..? N1 C5 C (6)..? C4 C5 C (7)..? C7 C6 C (8)..? C7 C6 C (8)..? C11 C6 C (7)..? C8 C7 C (9)..? C7 C8 C (8)..? C7 C8 Br (7)..? C9 C8 Br (7)..? C8 C9 C (8)..? C8 C9 C (9)..? C10 C9 C (9)..? C9 C10 C (9)..? C10 C11 C (7)..? C10 C11 Ir (6)..? C6 C11 Ir (5)..? N2 C13 C (7)..? C13 C14 C (7)..? C16 C15 C (7)..? C15 C16 C (7)..? N2 C17 C (6)..? N2 C17 C (6)..? C16 C17 C (7)..? C19 C18 C (7)..? C19 C18 C (7)..? C24 C18 C (6)..? C20 C19 C (7)..? C19 C20 C (7)..? C19 C20 Br (6)..? C21 C20 Br (6)..? C20 C21 C (7)..? C20 C21 C (7)..? C22 C21 C (7)..? C24 C22 C (7)..? C22 C24 C (7)..? C22 C24 Ir (5)..? C18 C24 Ir (5)..? N3 C25 C (7)..? C25 C26 C (8)..? C26 C27 C (7)..? C29 C28 C (7)..? C28 C29 N (7)..? C28 C29 C (6)..? N3 C29 C (6)..? C31 C30 C (7)..? C31 C30 C (6)..? C35 C30 C (6)..? C32 C31 C (7)..? C33 C32 C (7)..? C33 C32 Br (6)..? C31 C32 Br (6)..? C32 C33 C (7)..? C32 C33 C (7)..? C34 C33 C (7)..? C35 C34 C (7)..? 30
31 C30 C35 C (7)..? C30 C35 Ir (5)..? C34 C35 Ir (6)..? Cl1 C37 Cl (6) 2 3? Cl1 C37 Cl (6) 2.? Cl1 C37 Cl (6) 3.? Cl2 C38 Cl2 112(2). 6? Cl2 C38 Cl2 112(2). 11_554? Cl2 C38 Cl2 112(2) 6 11_554? Cl3 C39 Cl (9)..? Cl3 C39 Cl (9)..? Cl4 C39 Cl (10)..? #===END=========================================================== ============= 31
32 Table S5. The Parameters for X-ray Crystal Structure Analysis of 3b formula C 113 H 86 Cl 15 I 9 Ir 3 N 9 Mr crystal system cubic space group P2 1 3(#198) a (Å) (4) b (Å) (4) c (Å) (4) V (Å 3 ) (4) Z 4 D calc (g cm 3 ) μ (MoKα) (cm 1 ) R1 (I > 2σ(I)) wr2 (all reflections) No. of unique reflections 7347 (2θ < 57.4 ) The structure was solved by direct method and refined using least squares techniques (SHELXL97). 32
33 Table S6. Selected Bond Lengths of 3b. length (Å) length (Å) Ir(1) C(11) 2.008(7) Ir(1) N(1) 2.128(6) I(1) C(8) 2.090(10) N(1) C(1) 1.350(12) N(1) C(5) 1.374(12) C(1) C(2) 1.346(14) C(2) C(3) 1.401(15) C(3) C(4) 1.370(14) C(4) C(5) 1.398(14) C(5) C(6) 1.455(13) C(6) C(7) 1.420(13) C(6) C(11) 1.433(13) C(7) C(8) 1.387(14) C(8) C(9) 1.387(15) C(9) C(10) 1.402(14) C(9) C(12) 1.516(14) C(10) C(11) 1.401(13) Ir(2) C(23A) 1.984(9) Ir(2) C(23) 2.034(8) Ir(2) N(2A) 2.110(8) Ir(2) N(2) 2.141(7) I(2) C(20) 2.122(15) N(2) C(17) 1.363(14) N(2) C(13) 1.391(15) C(13) C(14) 1.392(16) C(14) C(15) 1.40(2) C(15) C(16) 1.38(2) C(16) C(17) 1.398(17) C(17) C(18) 1.488(19) C(18) C(23) 1.382(18) C(18) C(19) 1.391(17) C(19) C(20) 1.36(2) C(20) C(21) 1.42(3) C(21) C(22) 1.43(2) C(21) C(24) 1.52(2) C(22) C(23) 1.433(18) 33
34 I(2A) C(20A) 2.117(16) N(2A) C(17A) 1.358(15) N(2A) C(13A) 1.387(15) C(13A) C(14A) 1.395(16) C(14A) C(15A) 1.40(2) C(15A) C(16A) 1.38(2) C(16A) C(17A) 1.397(17) C(17A) C(18A) 1.487(19) C(18A) C(23A) 1.376(19) C(18A) C(19A) 1.394(18) C(19A) C(20A) 1.36(3) C(20A) C(21A) 1.42(3) C(21A) C(22A) 1.43(2) C(21A) C(24A) 1.51(3) C(22A) C(23A) 1.430(18) Ir(3) C(35) 2.011(7) Ir(3) N(3) 2.126(6) I(3) C(32) 2.124(9) N(3) C(25) 1.343(12) N(3) C(29) 1.378(12) C(25) C(26) 1.387(14) C(26) C(27) 1.358(15) C(27) C(28) 1.390(15) C(28) C(29) 1.400(14) C(29) C(30) 1.453(13) C(30) C(31) 1.394(13) C(30) C(35) 1.426(13) C(31) C(32) 1.373(14) C(32) C(33) 1.367(15) C(33) C(34) 1.419(13) C(33) C(36) 1.522(14) C(34) C(35) 1.397(12) C(37) Cl(1) 1.759(6) C(38) Cl(2) 1.758(11) C(39) Cl(3) C(39) Cl(5) C(39) Cl(4) C(39A) Cl(5A) C(39) Cl(3A) C(39) Cl(4A)
35 Table S7. Selected Bond Angles ( ) of 3b angle ( ) angle ( ) C(11) Ir(1) C(11) 94.8(3) C(11) Ir(1) C(11) 94.8(3) C(11) Ir(1) C(11) 94.8(3) C(11) Ir(1) N(1) 80.1(3) C(11) Ir(1) N(1) 174.6(3) C(11) Ir(1) N(1) 87.5(3) C(11) Ir(1) N(1) 87.5(3) C(11) Ir(1) N(1) 80.1(3) C(11) Ir(1) N(1) 174.6(3) N(1) Ir(1) N(1) 97.7(3) C(11) Ir(1) N(1) 174.6(3) C(11) Ir(1) N(1) 87.5(3) C(11) Ir(1) N(1) 80.1(3) N(1) Ir(1) N(1) 97.7(3) N(1) Ir(1) N(1) 97.7(3) C(1) N(1) C(5) 119.5(7) C(1) N(1) Ir(1) 126.0(6) C(5) N(1) Ir(1) 114.4(6) C(2) C(1) N(1) 123.1(9) C(1) C(2) C(3) 118.6(10) C(4) C(3) C(2) 119.4(9) C(3) C(4) C(5) 120.3(9) N(1) C(5) C(4) 119.0(8) N(1) C(5) C(6) 113.7(8) C(4) C(5) C(6) 127.3(9) C(7) C(6) C(11) 119.9(8) C(7) C(6) C(5) 122.8(9) C(11) C(6) C(5) 117.3(8) C(8) C(7) C(6) 118.8(9) C(9) C(8) C(7) 123.4(10) C(9) C(8) I(1) 118.8(7) C(7) C(8) I(1) 117.7(8) C(8) C(9) C(10) 116.8(9) C(8) C(9) C(12) 123.5(10) 35
36 C(10) C(9) C(12) 119.6(10) C(11) C(10) C(9) 123.6(9) C(10) C(11) C(6) 117.3(8) C(10) C(11) Ir(1) 128.5(7) C(6) C(11) Ir(1) 114.2(6) C(23A) Ir(2) C(23A) 95.2(10) C(23A) Ir(2) C(23A) 95.2(10) C(23A) Ir(2) C(23A) 95.2(10) C(23A) Ir(2) C(23) 9.6(9) C(23A) Ir(2) C(23) 88.0(7) C(23A) Ir(2) C(23) 102.3(10) C(23A) Ir(2) C(23) 102.3(10) C(23A) Ir(2) C(23) 9.6(9) C(23A) Ir(2) C(23) 88.0(7) C(23) Ir(2) C(23) 95.9(6) C(23A) Ir(2) C(23) 88.0(7) C(23A) Ir(2) C(23) 102.3(10) C(23A) Ir(2) C(23) 102.3(10) C(23A) Ir(2) C(23) 9.6(9) C(23A) Ir(2) C(23) 88.0(7) C(23) Ir(2) C(23) 95.9(6) C(23A) Ir(2) C(23) 88.0(7) C(23A) Ir(2) C(23) 102.3(10) C(23A) Ir(2) C(23) 9.6(9) C(23) Ir(2) C(23) 95.9(6) C(23) Ir(2) C(23) 95.9(6) C(23A) Ir(2) N(2A) 86.3(16) C(23A) Ir(2) N(2A) 174.9(11) C(23A) Ir(2) N(2A) 79.9(5) C(23) Ir(2) N(2A) 93.9(14) C(23) Ir(2) N(2A) 165.8(10) C(23) Ir(2) N(2A) 72.9(5) C(23A) Ir(2) N(2A) 79.9(5) C(23A) Ir(2) N(2A) 86.3(16) C(23A) Ir(2) N(2A) 174.9(11) C(23) Ir(2) N(2A) 72.9(5) C(23) Ir(2) N(2A) 93.9(14) C(23) Ir(2) N(2A) 165.8(10) N(2A) Ir(2) N(2A) 98.7(11) C(23A) Ir(2) N(2A) 174.9(11) 36
37 C(23A) Ir(2) N(2A) 79.9(5) C(23A) Ir(2) N(2A) 86.3(16) C(23) Ir(2) N(2A) 174.9(11) C(23) Ir(2) N(2A) 72.9(5) C(23) Ir(2) N(2A) 93.9(14) C(23A) Ir(2) N(2A) 165.8(10) N(2A) Ir(2) N(2A) 98.7(11) C(23A) Ir(2) N(2A) 174.9(11) C(23A) Ir(2) N(2A) 79.9(5) C(23A) Ir(2) N(2A) 86.3(16) C(23) Ir(2) N(2A) 165.8(10) C(23) Ir(2) N(2A) 72.9(5) C(23) Ir(2) N(2A) 93.9(14) N(2A) Ir(2) N(2A) 98.7(11) N(2A) Ir(2) N(2A) 98.7(11) C(23A) Ir(2) N(2) 177.4(9) C(23A) Ir(2) N(2) 84.5(5) C(23A) Ir(2) N(2) 87.4(12) C(23) Ir(2) N(2) 168.3(8) C(23) Ir(2) N(2) 77.7(5) C(23) Ir(2) N(2) 94.5(9) N(2A) Ir(2) N(2) 94.3(14) N(2A) Ir(2) N(2) 97.6(9) N(2A) Ir(2) N(2) 4.9(6) C(23A) Ir(2) N(2) 87.4(12) C(23A) Ir(2) N(2) 177.4(9) C(23A) Ir(2) N(2) 84.5(5) C(23) Ir(2) N(2) 94.5(9) C(23) Ir(2) N(2) 168.3(8) C(23) Ir(2) N(2) 77.7(5) N(2A) Ir(2) N(2) 4.9(6) N(2A) Ir(2) N(2) 94.3(14) N(2A) Ir(2) N(2) 97.5(9) N(2) Ir(2) N(2) 93.0(7) C(23A) Ir(2) N(2) 84.5(5) C(23A) Ir(2) N(2) 87.4(12) C(23A) Ir(2) N(2) 177.4(9) C(23) Ir(2) N(2) 77.7(5) C(23) Ir(2) N(2) 94.5(9) C(23) Ir(2) N(2) 168.3(8) 37
38 N(2A) Ir(2) N(2) 97.6(9) N(2A) Ir(2) N(2) 4.9(6) N(2A) Ir(2) N(2) 94.3(14) N(2) Ir(2) N(2) 93.0(7) N(2) Ir(2) N(2) 93.0(7) C(17) N(2) C(13) 117.7(9) C(17) N(2) Ir(2) N(2) C(13) C(14) 116.2(8) C(13) N(2) Ir(2) 126.1(8) 122.8(13) C(13) C(14) C(15) 118.0(13) C(16) C(15) C(14) 119.2(11) C(15) C(16) C(17) 121.2(12) N(2) C(17) C(16) 120.5(12) N(2) C(17) C(18) 112.8(10) C(16) C(17) C(18) 126.3(12) C(23) C(18) C(19) 123.9(14) C(23) C(18) C(17) 115.9(10) C(19) C(18) C(17) 120.2(13) C(20) C(19) C(18) 119.6(17) C(19) C(20) C(21) 121.6(14) C(19) C(20) I(2) 117.5(15) C(21) C(20) I(2) 120.8(13) C(20) C(21) C(22) 117.2(16) C(20) C(21) C(24) 124.1(16) C(22) C(21) C(24) 118.7(19) C(21) C(22) C(23) 121.5(17) C(18) C(23) C(22) 116.1(11) C(18) C(23) Ir(2) 117.3(9) C(22) C(23) Ir(2) 126.6(11) C(17A) N(2A) C(13A) 119.1(10) 38
39 39 C(17A) N(2A) Ir(2) N(2A) C(13A) C(14A) C(16A) C(15A) C(14A) N(2A) C(17A) C(16A) C(16A) C(17A) C(18A) C(23A) C(18A) C(17A) 114.2(8) 122.5(13) 119.9(12) 119.6(13) 127.3(13) 116.0(11) C(13A) N(2A) Ir(2) C(13A) C(14A) C(15A) C(15A) C(16A) C(17A) N(2A) C(17A) C(18A) C(23A) C(18A) C(19A) C(19A) C(18A) C(17A) 126.4(9) 117.4(14) 121.1(13) 113.0(10) 122.4(15) 120.7(14) C(20A) C(19A) C(18A) C(19A) C(20A) I(2A) C(20A) C(21A) C(22A) 118.9(17) 117.4(15) 116.6(16) C(19A) C(20A) C(21A) C(21A) C(20A) I(2A) C(20A) C(21A) C(24A) 122.8(15) 119.8(13) 124.3(17) C(22A) C(21A) C(24A) C(18A) C(23A) C(22A) 119(2) 117.7(13) C(21A) C(22A) C(23A) C(18A) C(23A) Ir(2) 120.2(17) 115.4(10) C(22A) C(23A) Ir(2) C(35) Ir(3) C(35) 124.3(11) 97.1(3) C(35) Ir(3) C(35) C(35) Ir(3) C(35) 97.1(3) 97.1(3) C(35) Ir(3) N(3) C(35) Ir(3) N(3) 89.7(3) 79.2(3) C(35) Ir(3) N(3) C(35) Ir(3) N(3) 172.6(4) 79.2(3) C(35) Ir(3) N(3) N(3) Ir(3) N(3) 89.7(3) 94.3(3) C(35) Ir(3) N(3) C(35) Ir(3) N(3) 172.6(4) 172.6(4) C(35) Ir(3) N(3) N(3) Ir(3) N(3) 79.2(3) 94.3(3) C(35) Ir(3) N(3) N(3) Ir(3) N(3) 89.7(3) 94.3(3)
40 C(25) N(3) C(29) 119.1(10) C(26) C(27) C(28) 119.6(10) C(27) C(28) C(29) 120.2(9) N(3) C(29) C(28) 119.1(8) N(3) C(29) C(30) 114.2(8) C(28) C(29) C(30) 126.6(9) C(31) C(30) C(35) 122.2(9) C(31) C(30) C(29) 122.0(8) C(35) C(30) C(29) 115.8(8) C(32) C(31) C(30) 119.4(9) C(33) C(32) C(31) 122.6(9) C(33) C(32) I(3) 121.0(7) C(31) C(32) I(3) 116.4(9) C(32) C(33) C(34) 116.6(9) C(32) C(33) C(36) 123.4(9) C(34) C(33) C(36) 120.0(9) C(35) C(34) C(33) 124.8(9) C(34) C(35) C(30) 114.2(7) C(34) C(35) Ir(3) 116.0(6) Cl(1) C(37) Cl(1) 110.5(5) Cl(1) C(37) Cl(1) 110.5(5) Cl(1) C(37) Cl(1) 110.5(5) Cl(2) C(38) Cl(2) 110.6(9) Cl(2) C(38) Cl(2) 110.6(9) Cl(2) C(38) Cl(2) 110.6(9) Cl(3) C(39) Cl(5) Cl(3) C(39) Cl(4) Cl(5) C(39) Cl(4) Cl(5A) C(39A) Cl(3A) Cl(5A) C(39A) Cl(4A) Cl(3A) C(39A) Cl(4A)
41 Table S8. CIF for the 3b # START VALIDATION REPLY FORM # VALIDATION REPLY FORM _verf_plat201_alert_2_a PLOBLEM: Isotropic non-h Atoms in Main Residue(s) RESPONSE: Disordered atoms, see _publ_section_exptl_refinement. #================================================================== ============ data_general _audit_creation_date ' ' _audit_creation_method 'by CrystalStructure 3.8' _audit_update_record? #================================================================== ============ # PROCESSING SUMMARY (IUCr Office Use Only) _journal_date_recd_electronic? _journal_date_from_coeditor? _journal_date_accepted? _journal_coeditor_code? #================================================================== ============ # SUBMISSION DETAILS _publ_contact_author_name 'ENTER NAME' _publ_contact_author_ 'ENTER ADDRESS' _publ_contact_author_fax 'ENTER FAX NUMBER' _publ_contact_author_phone 'ENTER PHONE NUMBER' _publ_contact_letter ENTER TEXT OF LETTER _publ_requested_journal test _publ_requested_category 'CHOOSE FI FM FO CI CM CO or AD' _publ_requested_coeditor_name? #================================================================== ============ # TITLE AND AUTHOR LIST _publ_section_title ENTER SECTION TITLE _publ_section_title_footnote ENTER FOOTNOTE TO TITLE OF PAPER loop publ_author_name 41
42 _publ_author_footnote _publ_author_address ' FIRST AUTHORS NAME ' FIRST AUTHORS FOOTNOTES FIRST AUTHORS ADDRESS _publ_section_synopsis ENTER SYNOPSIS #================================================================== ============ # TEXT _publ_section_abstract ENTER ABSTRACT _publ_section_comment ENTER TEXT _publ_section_references ENTER OTHER REFERENCES Johnson, C.K. (1976). ORTEP-II. A FORTRAN Thermal-Ellipsoid Plot Program. Report ORNL Oak Ridge National Laboratory, Tennessee, USA. Rigaku (1998). PROCESS-AUTO. Automatic Data Acquisition and Processing Package for Imaging Plate Diffractometer. Rigaku Corporation, Tokyo , Japan Rigaku & RAC (2007). CrystalStructure (Version 3.80). Single Crystal Structure Analysis Software. Rigaku, Tokyo , Japan. Rigaku Americas, TX, USA Sheldrick, G.M. (1997). SHELXS97. Program for the Solution of Crystal Structures. University of Gottingen, Germany. Sheldrick, G.M. (1997). SHELXL97. University of Gottingen, Germany. _publ_section_figure_captions ENTER FIGURE CAPTIONS _publ_section_exptl_prep ENTER COMPOUND PREPARATION DETAILS _publ_section_exptl_refinement One of ligands and chloroforms could be resolved with two disordered moieties, respectively. The atoms in the disordered portions were 42
43 heavily superimposed, so that they were refined isotropically. #================================================================== ============ data 7b (RGK1453) #================================================================== ============ # CHEMICAL DATA _chemical_formula_sum 'C37.67 H28.67 Cl5 I3 Ir N3 ' _chemical_formula_moiety 'C36 H27 I3 Ir1 N3, 1.67(C H Cl3) ' _chemical_formula_weight _chemical_melting_point? _chemical_absolute_configuration ad #================================================================== ============ # CRYSTAL DATA _symmetry_cell_setting cubic _symmetry_space_group_name_h-m 'P 21 3' _symmetry_space_group_name_hall 'P 2ac 2ab 3' _symmetry_int_tables_number 198 loop symmetry_equiv_pos_as_xyz 'x, y, z' 'y, z, x' 'z, x, y' 'x+1/2, -y+1/2, -z' 'y+1/2, -z+1/2, -x' 'z+1/2, -x+1/2, -y' '-y, z+1/2, -x+1/2' '-z, x+1/2, -y+1/2' '-z+1/2, -x, y+1/2' '-x+1/2, -y, z+1/2' '-y+1/2, -z, x+1/2' '-x, y+1/2, -z+1/2' # _cell_length_a (4) _cell_length_b (4) _cell_length_c (4) _cell_angle_alpha _cell_angle_beta _cell_angle_gamma _cell_volume (4) _cell_formula_units_z 12 _cell_measurement_reflns_used _cell_measurement_theta_min 3.6 _cell_measurement_theta_max 25.3 _cell_measurement_temperature # _exptl_crystal_description _exptl_crystal_colour 'block' 'yellow' 43
44 _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_diffrn _exptl_crystal_density_meas? _exptl_crystal_density_method 'not measured' _exptl_crystal_f_ _exptl_absorpt_coefficient_mu _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. _exptl_absorpt_correction_t_min _exptl_absorpt_correction_t_max #================================================================== ============ # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K a' _diffrn_radiation_wavelength _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method w _diffrn_detector_area_resol_mean _diffrn_reflns_number _diffrn_reflns_av_r_equivalents _diffrn_reflns_theta_max _diffrn_measured_fraction_theta_max _diffrn_reflns_theta_full _diffrn_measured_fraction_theta_full _diffrn_ambient_temperature _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 27 #================================================================== ============ # REFINEMENT DATA _refine_special_details Refinement was performed using all reflections. The weighted R-factor (wr) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(f^2^) is used only for calculating R-factor (gt). _reflns_number_total 7347 _reflns_number_gt 7133 _reflns_threshold_expression F^2^>2.0 s(f^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_r_factor_gt _refine_ls_wr_factor_ref _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns
45 _refine_ls_number_parameters 425 _refine_ls_goodness_of_fit_ref _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[ s^2^(fo^2^)+(0.0470p)^2^ p] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_shift/su_max _refine_diff_density_max 2.58 _refine_diff_density_min _refine_ls_extinction_method none _refine_ls_extinction_coef? _refine_ls_abs_structure_details 'Flack, H. D. (1983), Acta Cryst. A39, Friedel Pairs' _refine_ls_abs_structure_flack 0.016(8) loop atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' International Tables for Crystallography (1992, Vol. C, Tables and ) 'H' 'H' International Tables for Crystallography (1992, Vol. C, Table ) 'Cl' 'Cl' International Tables for Crystallography (1992, Vol. C, Tables and ) 'I' 'I' International Tables for Crystallography (1992, Vol. C, Tables and ) 'Ir' 'Ir' International Tables for Crystallography (1992, Vol. C, Tables and ) 'N' 'N' International Tables for Crystallography (1992, Vol. C, Tables and ) #================================================================== ============ # ATOMIC COORDINATES AND THERMAL PARAMETERS loop atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y 45
46 _atom_site_fract_z _atom_site_u_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ir1 Ir (15) (15) (15) (14) Uani 1 3 d SDU.. I1 I (3) (4) (4) (2) Uani 1 1 d U.. N1 N (3) (3) (3) (14) Uani 1 1 d DU.. C1 C (4) (4) (4) (17) Uani 1 1 d U.. H1 H Uiso 1 1 calc R.. C2 C (5) (4) (5) (19) Uani 1 1 d U.. H2 H Uiso 1 1 calc R.. C3 C (5) (4) (4) (18) Uani 1 1 d U.. H3 H Uiso 1 1 calc R.. C4 C (4) (4) (4) (18) Uani 1 1 d U.. H4 H Uiso 1 1 calc R.. C5 C (4) (4) (4) (15) Uani 1 1 d U.. C6 C (4) (4) (4) (16) Uani 1 1 d U.. C7 C (4) (4) (4) (17) Uani 1 1 d U.. H7 H Uiso 1 1 calc R.. C8 C (4) (4) (5) (18) Uani 1 1 d U.. C9 C (4) (4) (5) (17) Uani 1 1 d U.. C10 C (4) (4) (4) (17) Uani 1 1 d U.. H10 H Uiso 1 1 calc R.. C11 C (3) (4) (4) (16) Uani 1 1 d DU.. C12 C (5) (6) (6) 0.041(2) Uani 1 1 d U.. H12A H Uiso 1 1 calc R.. H12B H Uiso 1 1 calc R.. H12C H Uiso 1 1 calc R.. Ir2 Ir (16) (16) (16) (15) Uani 1 3 d SD.. I2 I (19) (2) (10) (12) Uani 0.616(6) 1 d PDU A 1 N2 N (4) (11) (5) 0.021(3) Uiso 0.616(6) 1 d PDU A 1 C13 C (6) (10) (7) 0.024(3) Uiso 0.616(6) 1 d PDU A 1 H13 H Uiso 0.616(6) 1 calc PR A 1 C14 C (6) (8) (8) 0.027(3) Uiso 0.616(6) 1 d PDU A 1 H14 H Uiso 0.616(6) 1 calc PR A 1 C15 C (6) (7) (8) 0.023(3) Uiso 0.616(6) 1 d PDU A 1 H15 H Uiso 0.616(6) 1 calc PR A 1 C16 C (6) (8) (7) 0.023(3) Uiso 0.616(6) 1 d PDU A 1 H16 H Uiso 0.616(6) 1 calc PR A 1 C17 C (6) (10) (6) 0.025(3) Uiso 0.616(6) 1 d PDU A 1 C18 C (7) (10) (6) 0.026(3) Uiso 0.616(6) 1 d PDU A 1 C19 C (9) (9) (6) 0.033(3) Uiso 0.616(6) 1 d PDU A 1 H19 H Uiso 0.616(6) 1 calc PR A 1 C20 C (10) (9) (7) 0.037(3) Uiso 0.616(6) 1 d PDU A 1 C21 C (10) (9) (8) 0.038(3) Uiso 0.616(6) 1 d PDU A 1 C22 C (8) (9) (7) 0.035(3) Uiso 0.616(6) 1 d PDU A 1 H22 H Uiso 0.616(6) 1 calc PR A 1 C23 C (7) (9) (4) 0.029(3) Uiso 0.616(6) 1 d PDU A 1 C24 C (9) (9) (9) 0.047(4) Uiso 0.616(6) 1 d PDU A 1 H24A H Uiso 0.616(6) 1 calc PR A 1 H24B H Uiso 0.616(6) 1 calc PR A 1 H24C H Uiso 0.616(6) 1 calc PR A 1 I2A I (3) (14) (13) (13) Uani 0.384(6) 1 d PDU A 2 N2A N (6) (19) (8) 0.023(4) Uiso 0.384(6) 1 d PDU A 2 C13A C (8) (16) (8) 0.023(4) Uiso 0.384(6) 1 d PDU A 2 H13A H Uiso 0.384(6) 1 calc PR A 2 46
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